1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (8aS)- supplier

Name
(S)-(+)-3,4,8,8A-TETRAHYDRO-8A-METHYL-1,6(2H,7H)-NAPHTHALENEDIONE
EINECS
CAS No. 33878-99-8
Article Data103
CAS DataBase
Density 1.1 g/cm³
Solubility
Melting Point 50-52 °C(lit.)
Formula C₁₁H₁₄O₂
Boiling Point 325.5 °C at 760 mmHg
Molecular Weight 178.231
Flash Point 122 °C
Transport Information
Appearance
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (S)-;1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (S)-(+)- (8CI);(+)-Wieland-Miescher ketone;(S)-1,2,3,4,6,7,8,8a-Octahydro-8a-methyl-1,6-naphthalenedione;(S)-Wieland-Miescher ketone;
PSA 34.14000
LogP 2.03500

Synthetic route

: 878-47-7, 4242-00-6, 34996-06-0, 50302-16-4, 70191-02-5, 34996-05-9
(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 17h; enantioselective reaction;	97.9%
With jones reagent Oxidation;

: 5073-65-4
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions

Conditions	Yield
With N-tosyl-(Sa)-1,1'-binaphthyl-2,2'-diamine-L-prolinamide; benzoic acid at 25℃; for 27h; Neat (no solvent); optical yield given as %ee; enantioselective reaction;	95%
With N-tosyl-(Sa)-1,1'-binaphthyl-2,2'-diamine-L-prolinamide; benzoic acid for 168h; optical yield given as %ee; enantioselective reaction;	94%
With L-proline at 20℃; for 2h; Catalytic behavior; Aldol Condensation; Ionic liquid; enantioselective reaction;	88%

: 174851-52-6
14-noreudesma-4,11-dien-3,9-dione

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions

Conditions	Yield
Stage #1: 14-noreudesma-4,11-dien-3,9-dione With methanol; ozone Stage #2: With ferrous(II) sulfate heptahydrate; thiophenol at -78 - 20℃; for 0.5h;	91%

: 5073-65-4
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

A: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B: 100348-93-4
(R)-Wieland-Miescher ketone

Conditions

Conditions	Yield
With L-proline at 20℃; for 2h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst; Aldol Condensation; Ionic liquid; enantioselective reaction;	A 78% B n/a
With (S)-2-(1-pyrrolidinylmethyl)pyrrolidine In dimethyl sulfoxide at 20℃; for 10h; Hajos-Parrish-Eder-Sauer-Wiechert reaction; optical yield given as %ee; enantioselective reaction;	A 55% B n/a
With (S)-2-(1-pyrrolidinylmethyl)pyrrolidine; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 48h; Hajos-Parrish-Eder-Sauer-Wiechert reaction; optical yield given as %ee; enantioselective reaction;	A n/a B 52%

: 5073-65-4
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

A: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B: 20007-99-2, 33878-99-8, 100348-93-4, 20007-72-1
Wieland-Miescher ketone

Conditions

Conditions	Yield
L-proline In N,N-dimethyl-formamide for 168h; Ambient temperature;	A 36% B 42%

: 20007-99-2, 33878-99-8, 100348-93-4, 20007-72-1
Wieland-Miescher ketone

A: 9a-methyl-4,5,9,9a-tetrahydro-3H,8H-benzo[b]oxepine-2,7-dione

B: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

C: 100348-93-4
(R)-Wieland-Miescher ketone

D: 257941-62-1
(-)-(4aR,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Conditions

Conditions	Yield
With α-D-glucose 6-phosphate; oxygen; NADP; glucose-6-phosphate dehydrogenase; recombinant c-hexanone monooxygenase (E. coli TOP10 pQR239) In phosphate buffer at 20℃; for 26h; pH=8.7; Baeyer-Villiger oxidation; Further byproducts given;	A 35% B n/a C n/a D n/a

...Expand

: 5073-65-4
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

A: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B: N-[4-((R)-6-Fluoro-3-hydroxy-5-oxo-hexyl)-phenyl]-acetamide

C: N-[4-((3R,4S)-4-Fluoro-3-hydroxy-5-oxo-hexyl)-phenyl]-acetamide

Conditions

Conditions	Yield
With antibody 38C2; PBS buffer In 1,2-dimethoxyethane for 504h; Ambient temperature; Yields of byproduct given. Title compound not separated from byproducts;	A n/a B 7% C n/a

...Expand

: 5073-65-4
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

A: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B: 5004-80-8
6-hydroxy-1,6-dimethylbicyclo<3.3.1>nonane-2,9-dione

C: 100348-93-4
(R)-Wieland-Miescher ketone

Conditions

Conditions	Yield
With L-proline In N,N-dimethyl-formamide for 24h; Ambient temperature; Yield given. Title compound not separated from byproducts;

...Expand

: 51547-30-9
5β-hydroxy-5α-ethynyl-10β-methyl-Δ1(9)-octalin-2-one

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions

Conditions	Yield
With silver carbonate In dimethyl sulfoxide

: 20007-99-2, 33878-99-8, 100348-93-4, 20007-72-1
Wieland-Miescher ketone

A: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B: 257941-62-1
(-)-(4aR,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Conditions

Conditions	Yield
With D-glucose; yeast cells of Candida melibiosica IAM4488 In phosphate buffer at 30℃; for 68h; pH=6.5; Reduction; Enzymatic reaction;

: 20007-99-2, 33878-99-8, 100348-93-4, 20007-72-1
Wieland-Miescher ketone

A: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B: 100348-93-4
(R)-Wieland-Miescher ketone

Conditions

Conditions	Yield
Kinetic resolution; baker's yeast reduction; Title compound not separated from byproducts;
In hexane; isopropyl alcohol Reagent/catalyst; Resolution of racemate;

: 1193-55-1
2-methylcyclohexane-1,3-dione

: 78-94-4
methyl vinyl ketone

A: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B: 100348-93-4
(R)-Wieland-Miescher ketone

Conditions

Conditions	Yield
With L-proline In dimethyl sulfoxide at 35℃; for 89h; Product distribution; Further Variations:; Reagents; Addition;
With L-proline In dimethyl sulfoxide at 35℃; for 89h; Addition; Title compound not separated from byproducts;
Stage #1: 2-methylcyclohexane-1,3-dione With L-proline In dimethyl sulfoxide at 15 - 25℃; for 6h; Stage #2: methyl vinyl ketone In dimethyl sulfoxide at 15 - 25℃; for 180h; asymmetric Robinson annulation; Stage #3: With pyridinium p-toluenesulfonate In benzene for 2h; Heating; Title compound not separated from byproducts;

...Expand

: 5073-65-4
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

: (+/-)-(4aS,6S,8aS)-6,8a-dimethylhexahydro-2H-chromene-2,5(3H)-dione

: (+/-)-(4aS,6R,8aS)-6,8a-dimethylhexahydro-2H-chromene-2,5(3H)-dione

C: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions

Conditions	Yield
With water In acetonitrile Heating; Title compound not separated from byproducts.;

...Expand

: 5073-65-4
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

A: C11H14O(18)O

B: C11H14(18)O2

C: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions

Conditions	Yield
With water; 18O-labeled water In acetonitrile at 80℃; Title compound not separated from byproducts.;

...Expand

: 1193-55-1
2-methylcyclohexane-1,3-dione

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 20 °C 2: (S)-5,6-dimethyl-2-(pyrrolidin-2-yl)-1H-benzimidazole; TFA / tetrahydrofuran / 48 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: (S)-2-diphenylmethyl-pirrolidine 2: L-proline / 120 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: H2O 2: (i) aq. HClO4, L-proline, MeCN, (ii) /BRN= 969178/, liq. NH3, Et2O 3: Ag2CO3 / dimethylsulfoxide View Scheme

: 20007-99-2, 33878-99-8, 100348-93-4, 20007-72-1
Wieland-Miescher ketone

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: yeast cells of Toluraspora delbrueckii IFO 10921; glucose / aq. phosphate buffer / 30 °C / pH 6.5 / Enzymatic reaction 2: Jones reagent View Scheme
Multi-step reaction with 2 steps 1: NADPH; glucose dehydrogenase; 7α-hydroxysteroid dehydrogenase from extremophilic bacterium Deinococcus marmoris strain / aq. phosphate buffer; dimethyl sulfoxide / 25 °C / Enzymatic reaction 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 17 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: NADPH; glucose dehydrogenase; IS2-SDR from Icelandic hot spring sediments / aq. phosphate buffer; dimethyl sulfoxide / 25 °C / Enzymatic reaction 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 17 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / ethanol / 4 h / 0 °C 2: Amano Lipase PS / acetone / 144 h / 45 °C / Enzymatic reaction 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 17 h / 20 °C View Scheme

: 5073-65-4
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

A: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B: 100348-93-4
(R)-Wieland-Miescher ketone

C: 35537-88-3
cis-9-Hydroxy-10-methyl-dekalin-2,5-dion

Conditions

Conditions	Yield
With (S)-N-(4-nitrophenyl)pyrrolidine-2-carboxamide In chloroform at 20℃; Hajos-Parrish reaction; optical yield given as %ee; enantioselective reaction;

...Expand

: 5073-65-4
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

A: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B: 35537-88-3
cis-9-Hydroxy-10-methyl-dekalin-2,5-dion

Conditions

Conditions	Yield
With (S)-N-(3,5-bis(trifluoromethyl)phenyl)pyrrolidine-2-carboxamide In chloroform at 20℃; Hajos-Parrish reaction; optical yield given as %ee; enantioselective reaction;
With formic acid; (S)-N-{3,6-dichloro-8-[N-(2,4,4-trimethylpentan-2-yl)sulfamoyl]-9H-carbazol-1-yl}pyrrolidine-2-carboxamide formate In chloroform-d1 at 20℃; for 130h; enantioselective reaction;	A n/a B n/a

: 1193-55-1
2-methylcyclohexane-1,3-dione

: 78-94-4
methyl vinyl ketone

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions

Conditions	Yield
With L-proline Robinson annulation;

: 5073-65-4
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

: 108-94-1
cyclohexanone

A: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B: 100348-93-4
(R)-Wieland-Miescher ketone

Conditions

Conditions	Yield
With 4-nitro-benzoic acid In water at 22℃; for 24h; Aldol condensation; optical yield given as %ee; enantioselective reaction;

...Expand

: 1193-55-1
2-methylcyclohexane-1,3-dione

A: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B: 100348-93-4
(R)-Wieland-Miescher ketone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / 3 h / Inert atmosphere 2: benzoic acid / neat (no solvent) / 120 h / 25 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 12 h 2: acetic acid / water / 120 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid; hydroquinone / water / 80 °C 2: L-proline / dimethyl sulfoxide / 120 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: lipase AS / acetone; dimethyl sulfoxide / 192 h / 10 °C / Inert atmosphere; Enzymatic reaction 2: toluene-4-sulfonic acid / acetone; dimethyl sulfoxide / 2 h / 10 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: triethylamine / neat (no solvent) / 16 h / 20 °C 2: (R)-pyrrolidine-2-(N-(3,5-bis(trifluoromethyl)phenyl)carboxamide) / chloroform / 168 h / 20 °C / Inert atmosphere View Scheme

: 35537-88-3
cis-9-Hydroxy-10-methyl-dekalin-2,5-dion

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions

Conditions	Yield
In diethyl ether at -20℃;	101.2 g

: 4242-00-6
(±)-4a,5-cis-(5-hydroxy-4a-methyl-4,4 a,5,6,7,8-hexahydronaphthalen-2(3H)-one)

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Amano Lipase PS / acetone / 144 h / 45 °C / Enzymatic reaction 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 17 h / 20 °C View Scheme

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 878-47-7, 4242-00-6, 34996-06-0, 50302-16-4, 70191-02-5, 34996-05-9
(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol; dichloromethane at -78℃; for 0.25h; chemoselective reaction;	100%
With sodium tetrahydroborate In methanol at 0℃; for 0.5h;	97%
With sodium tetrahydroborate In ethanol at 0℃;	97%

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 540-63-6
ethane-1,2-dithiol

: 145632-33-3
(S)-7a′-methyl-2′,3′,7′,7a′-tetrahydrospiro[[1,3]dithiolane-2,5′-inden]-1′(6′H)-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid for 5h; Ambient temperature;	99%
With toluene-4-sulfonic acid In acetic acid for 6h;	93%
With toluene-4-sulfonic acid In acetic acid for 5h; Ambient temperature;	92%

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 201012-67-1
(1S,6R)-1-methylbicyclo[4.4.0]decane-2,8-dione

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In hydrogenchloride; ethanol	98%
With glucose-6-phosphate dehydrogenase; metagenomic ene-reductase from pQR1907; β-D-glucose-6-phosphate sodium salt; NADPH In dimethyl sulfoxide at 30℃; for 20h; pH=7.4; Reagent/catalyst; Enzymatic reaction; stereoselective reaction;	95%
Multi-step reaction with 2 steps 1.1: 5%-palladium/activated carbon; palladium dichloride; hydrogen / 0.25 h / 20 °C 1.2: 48 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 h / 70 °C View Scheme
With palladium on activated carbon; hydrogen In ethyl acetate at 20℃; for 2h;

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 107-21-1
ethylene glycol

: 61950-54-7
(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 0.916667h; Heating;	96.7%
In toluene for 5h; Heating;	95%
With 4 A molecular sieve; toluene-4-sulfonic acid at 20℃; for 0.383333h;	93%

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 917-54-4
methyllithium

: 163955-62-2
cis-4a,8a-dimethyloctahydro-2(1H),5(6H)-dione

Conditions

Conditions	Yield
With copper(l) iodide In diethyl ether at 0 - 20℃;	96%

: 126-39-6
2-ethyl-2-methyl-1,3-dioxolane

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 61950-54-7
(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethylene glycol Inert atmosphere; regioselective reaction;	95%
With toluene-4-sulfonic acid; ethylene glycol	94%
With toluene-4-sulfonic acid In ethylene glycol for 30h; Ambient temperature;	79%
With toluene-4-sulfonic acid
With toluene-4-sulfonic acid In ethylene glycol

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 107-21-1
ethylene glycol

: 98540-60-4
(S)-4a-methyl-4,4a,6,7-tetrahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolan]-5(3H)-one

Conditions

Conditions	Yield
With 2,4,6-collidinium p-toluenesulfonate Inert atmosphere; Reflux;	93%

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 358-23-6
trifluoromethylsulfonic anhydride

: Trifluoro-methanesulfonic acid (S)-4a-methyl-5-oxo-3,4,4a,5,6,7-hexahydro-naphthalen-2-yl ester

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 0 - 20℃; for 1h;	88%

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: (S)-8a-Methyl-hexahydro-naphthalene-1,6-dione

Conditions

Conditions	Yield
With hydrogen; <((t-Bu)2PH)PdP(t-Bu)2>2 saturated with oxygen In tetrahydrofuran under 760 Torr; for 12h; Ambient temperature;	83%

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 34996-06-0
(R)-1,2,3,4,8,8a-hexahydro-1β-hydroxy-8aβ-methyl-6-(7H)-naphthalenone

Conditions

Conditions	Yield
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione With sodium tetrahydroborate In ethanol at 0℃; for 3.5h; Stage #2: With acetic acid In ethanol	81%

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 108-24-7
acetic anhydride

A: (S)-4a-methyl-5-oxo-3,4,4a,5,6,7-hexahydronaphthalen-2-yl acetate

B: C15H18O4

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 115℃; for 5.5h; Inert atmosphere;	A 81% B 18%

...Expand

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 126-30-7
2,2-Dimethyl-1,3-propanediol

: 42829-94-7, 105394-94-3
(dimethyl-2,2 propanediyldioxy-1,3)-1,1 methyl-8a octahydro-1,2,3,4,6,7,8,8a oxo-6 naphtalene

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether at 0℃; for 5h;	80%

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 18162-48-6
tert-butyldimethylsilyl chloride

A: 274914-64-6
5-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

B: (4S,4aS)-4,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-1,2,3,4,4a,5,6,7-octahydro-naphthalene

Conditions

Conditions	Yield
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione With sodium tetrahydroborate In methanol; dichloromethane at -78℃; Reduction; Stage #2: tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide at 45℃; Etherification;	A 75% B 10%

...Expand

: 75-77-4
chloro-trimethyl-silane

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 917-54-4
methyllithium

: (5S,9R,10S)-5,10-dimethyl-4,8-dioxo-9-trimethylsilyloxydecalin

Conditions

Conditions	Yield
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione; methyllithium With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; chloro-trimethyl-silane In 1,2-dimethoxyethane; diethyl ether at 0℃; for 1h; Inert atmosphere; Stage #2: With Oxone; 18-crown-6 ether; sodium hydrogencarbonate In dichloromethane; water; acetone at 0℃; for 1h; Inert atmosphere; Stage #3: chloro-trimethyl-silane In pyridine Inert atmosphere;	75%

Yield

Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione; methyllithium With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; chloro-trimethyl-silane In 1,2-dimethoxyethane; diethyl ether at 0℃; for 1h; Inert atmosphere;
Stage #2: With Oxone; 18-crown-6 ether; sodium hydrogencarbonate In dichloromethane; water; acetone at 0℃; for 1h; Inert atmosphere;
Stage #3: chloro-trimethyl-silane In pyridine Inert atmosphere;

75%

...Expand

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 7381-30-8
2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

A: 61950-54-7
(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene

B: 98576-57-9
C15H22O4

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - -10℃; for 8.5h;	A 73% B 6.3%
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 8.5h;	A 73% B 6.3%

...Expand

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 358-23-6
trifluoromethylsulfonic anhydride

: 174617-50-6
Trifluoro-methanesulfonic acid (S)-8a-methyl-6-oxo-3,4,6,7,8,8a-hexahydro-naphthalen-1-yl ester

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 0 - 20℃; for 1.5h;	70%

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 145100-51-2
N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

A: Trifluoro-methanesulfonic acid (S)-4a-methyl-5-oxo-4,4a,5,6,7,8-hexahydro-naphthalen-2-yl ester

B: Trifluoro-methanesulfonic acid (S)-4a-methyl-5-oxo-3,4,4a,5,6,7-hexahydro-naphthalen-2-yl ester

C: Trifluoro-methanesulfonic acid (S)-8a-methyl-6-trifluoromethanesulfonyloxy-3,4,8,8a-tetrahydro-naphthalen-1-yl ester

D: 174617-50-6
Trifluoro-methanesulfonic acid (S)-8a-methyl-6-oxo-3,4,6,7,8,8a-hexahydro-naphthalen-1-yl ester

Conditions

Conditions	Yield
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 3h; Stage #2: N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide In tetrahydrofuran at 20℃; for 1h;	A 4.5% B 2.3% C 5.3% D 69%

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: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 2450-71-7
Propargylamine

: 6a-methyl-6,6a,8,9-tetrahydrobenzo[f]quinolin-7(5H)-one

Conditions

Conditions	Yield
sodium tetrachloroaurate dihydrate In ethanol at 78℃; for 24h;	68%

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 29689-53-0
6a-methyl-6,6a,9,10-tetrahydro-5H-tetrazolo<5,1-b><3>benzazepin-7(8H)-one

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide In dichloromethane for 18h; Ambient temperature;	67%

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 7381-30-8
2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

A: 61950-54-7
(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene

B: 98540-60-4
(S)-4a-methyl-4,4a,6,7-tetrahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolan]-5(3H)-one

C: 98576-57-9
C15H22O4

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 51h; Yields of byproduct given;	A n/a B 65% C n/a

...Expand

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 814-49-3
diethyl chlorophosphate

A: Phosphoric acid diethyl ester (S)-4a-methyl-5-oxo-3,4,4a,5,6,7-hexahydro-naphthalen-2-yl ester

B: Phosphoric acid diethyl ester (S)-8a-methyl-6-oxo-3,4,6,7,8,8a-hexahydro-naphthalen-1-yl ester

Conditions

Conditions	Yield
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 2.5h; Stage #2: diethyl chlorophosphate In tetrahydrofuran at 20℃; for 0.416667h;	A 4% B 61%

...Expand

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 107-21-1
ethylene glycol

: 101053-28-5
(1S,6R)-8,8-ethylenedioxy-1-methylbicyclo[4.4.0]decan-2-one

Conditions

Conditions	Yield
Stage #1: ethylene glycol With 5%-palladium/activated carbon; hydrogen; palladium dichloride at 20℃; for 0.25h; Stage #2: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione In tetrahydrofuran at 20℃; for 48h;	60%

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 2524-64-3
chlorophosphoric acid diphenyl ester

A: Phosphoric acid (S)-4a-methyl-5-oxo-4,4a,5,6,7,8-hexahydro-naphthalen-2-yl ester diphenyl ester

B: Phosphoric acid (S)-8a-methyl-6-oxo-3,4,6,7,8,8a-hexahydro-naphthalen-1-yl ester diphenyl ester

C: Phosphoric acid (S)-5-(diphenoxy-phosphoryloxy)-4a-methyl-4,4a,7,8-tetrahydro-naphthalen-2-yl ester diphenyl ester

Conditions

Conditions	Yield
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Stage #2: chlorophosphoric acid diphenyl ester In tetrahydrofuran at 0℃; for 0.333333h;	A 19% B 53% C 5%

...Expand

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 814-49-3
diethyl chlorophosphate

A: Phosphoric acid diethyl ester (S)-4a-methyl-5-oxo-4,4a,5,6,7,8-hexahydro-naphthalen-2-yl ester

B: Phosphoric acid diethyl ester (S)-8a-methyl-6-oxo-3,4,6,7,8,8a-hexahydro-naphthalen-1-yl ester

C: Phosphoric acid (S)-5-(diethoxy-phosphoryloxy)-4a-methyl-4,4a,7,8-tetrahydro-naphthalen-2-yl ester diethyl ester

Conditions

Conditions	Yield
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Stage #2: diethyl chlorophosphate In tetrahydrofuran at 0℃; for 0.333333h;	A 16% B 50% C 14%

...Expand

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 107-21-1
ethylene glycol

: 119772-90-6
(S)-4'a-Methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one

Conditions

Conditions	Yield
With 2,4,6-collidinium p-toluenesulfonate In toluene for 48h; Inert atmosphere; Reflux;	44%

1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (8aS)- Specification

The CAS register number of 1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (8aS)- is 33878-99-8. It also can be called as 1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (S)- and the systematic name about this chemical is (8aS)-8a-methyl-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione. The molecular formula about this chemical is C₁₁H₁₄O₂ and the molecular weight is 178.23.

Physical properties about 1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (8aS)- are: (1)ACD/LogP: 0.85; (2)#H bond acceptors: 2; (3)Polar Surface Area: 34.14 Å²; (4)Index of Refraction: 1.519; (5)Molar Refractivity: 48.81 cm³; (6)Molar Volume: 160.7 cm³; (7)Polarizability: 19.35x10^-24cm³; (8)Surface Tension: 39.1 dyne/cm; (9)Density: 1.1 g/cm³; (10)Flash Point: 122 °C; (11)Enthalpy of Vaporization: 56.77 kJ/mol; (12)Boiling Point: 325.5 °C at 760 mmHg; (13)Vapour Pressure: 0.000229 mmHg at 25 °C.

When you are using this chemical, please be cautious about it as the following:
When you are using this chemical, avoid contact with skin and eyes and do not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1CCC/C2=C/C(=O)CC[C@]12C
(2)InChI: InChI=1/C11H14O2/c1-11-6-5-9(12)7-8(11)3-2-4-10(11)13/h7H,2-6H2,1H3/t11-/m0/s1
(3)InChIKey: DNHDRUMZDHWHKG-NSHDSACABU
(4)Std. InChI: InChI=1S/C11H14O2/c1-11-6-5-9(12)7-8(11)3-2-4-10(11)13/h7H,2-6H2,1H3/t11-/m0/s1
(5)Std. InChIKey: DNHDRUMZDHWHKG-NSHDSACASA-N

Product Name

(S)-(+)-3,4,8,8A-TETRAHYDRO-8A-METHYL-1,6(2H,7H)-NAPHTHALENEDIONE

Synthetic route

1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (8aS)- Specification

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